Mickey Drexler is an American retail icon
-President of The Gap at age 39
-Takes it from 450 stores to 4,000
-Steve Jobs got him to Design the Apple Store
-Started Old Navy
-Ran J. Crew
Perhaps the most brilliant retail mind ever.
We sat down for an unfiltered conversation:
-President of The Gap at age 39
-Takes it from 450 stores to 4,000
-Steve Jobs got him to Design the Apple Store
-Started Old Navy
-Ran J. Crew
Perhaps the most brilliant retail mind ever.
We sat down for an unfiltered conversation:
Mickey on Making it in America Without Connections
I want to start by saying that Mickey Drexler came from nothing.
He grew up in the Bronx with no money or connections, and his father made $15k/year.
Mickey made it work in the 1960s, but I asked him if the same thing holds true now.
What's someone supposed to do in today’s world if they’re smart, ambitious, but don’t come from wealth and don’t have a great network?
Mickey dove right in.
I quickly realized that Mickey likes to answer questions by telling stories to drive home his messages.
He told me that while we was running The Gap, he had a chance to tour a high school in Harlem.
While walking through the hallway that day, a teenager approached him out of nowhere and asked who he was and what he was doing there.
He could sense her confidence and energy right away.
He could tell within seconds of speaking with her that she was a natural leader.
That she was curious. She just had it.
So, Mickey hired her to work at The Gap that summer.
This was just one example of the countless times he would unexpectedly come across somebody in day-to-day life and get a feel for that person’s talent right away.
That was the lesson. Many great leaders have an uncanny ability to spot talent instantly, and are always on the lookout to recruit the next standout.
You don’t always need a formal interview or a fancy degree to get in front of the right people and make an impression quickly.
You just need to create interactions with as many people as you can, as you never know who that person is that you just approached.
If you have it – they will see it.
So, what ever happened to that 16-year-old girl from Harlem that Mickey hired for that summer job all those years ago?
Yandy Smith is now known to millions around the world as the star of Love & Hip Hop, and has had a storied career as an entrepreneur, singer, and actress.
Mickey's instincts were correct.
I want to start by saying that Mickey Drexler came from nothing.
He grew up in the Bronx with no money or connections, and his father made $15k/year.
Mickey made it work in the 1960s, but I asked him if the same thing holds true now.
What's someone supposed to do in today’s world if they’re smart, ambitious, but don’t come from wealth and don’t have a great network?
Mickey dove right in.
I quickly realized that Mickey likes to answer questions by telling stories to drive home his messages.
He told me that while we was running The Gap, he had a chance to tour a high school in Harlem.
While walking through the hallway that day, a teenager approached him out of nowhere and asked who he was and what he was doing there.
He could sense her confidence and energy right away.
He could tell within seconds of speaking with her that she was a natural leader.
That she was curious. She just had it.
So, Mickey hired her to work at The Gap that summer.
This was just one example of the countless times he would unexpectedly come across somebody in day-to-day life and get a feel for that person’s talent right away.
That was the lesson. Many great leaders have an uncanny ability to spot talent instantly, and are always on the lookout to recruit the next standout.
You don’t always need a formal interview or a fancy degree to get in front of the right people and make an impression quickly.
You just need to create interactions with as many people as you can, as you never know who that person is that you just approached.
If you have it – they will see it.
So, what ever happened to that 16-year-old girl from Harlem that Mickey hired for that summer job all those years ago?
Yandy Smith is now known to millions around the world as the star of Love & Hip Hop, and has had a storied career as an entrepreneur, singer, and actress.
Mickey's instincts were correct.
Mickey on a College Degree
Although Mickey believes that true learning doesn’t happen in college, he thinks a degree is critical.
For one, the social skills that college helps develop are critical. But beyond that, a harsh reality:
As is the case with many companies, Mickey rarely gets a chance to formally interview folks without degrees, as few ever get through the screening process that allow them to get to him in the first place.
Does it matter where somebody went to college?
Not really, but he believes some universities produce a greater percentage of graduates with a sense of entitlement, A MAJOR pet-peeve of Mickey’s.
He thinks that feeling the world owes you something is a huge barrier to success, and terrible for company culture.
He also warns graduates about chasing jobs for the sake of prestige and money, and highlights the fact many end up working countless hours in jobs they find boring and don’t like, but stay hooked only because of the financial incentives.
Big school or small, gotta keep that sense of humility.
Although Mickey believes that true learning doesn’t happen in college, he thinks a degree is critical.
For one, the social skills that college helps develop are critical. But beyond that, a harsh reality:
As is the case with many companies, Mickey rarely gets a chance to formally interview folks without degrees, as few ever get through the screening process that allow them to get to him in the first place.
Does it matter where somebody went to college?
Not really, but he believes some universities produce a greater percentage of graduates with a sense of entitlement, A MAJOR pet-peeve of Mickey’s.
He thinks that feeling the world owes you something is a huge barrier to success, and terrible for company culture.
He also warns graduates about chasing jobs for the sake of prestige and money, and highlights the fact many end up working countless hours in jobs they find boring and don’t like, but stay hooked only because of the financial incentives.
Big school or small, gotta keep that sense of humility.
Mickey on the un-mentor, and Smelling BS
Mickey is quick to note that he never had a mentor, and that he had to learn to trust his own instincts.
He also learned early on that he had an ability to identify BS very quickly -- a skill he thinks is incredibly important for success.
He has a great admiration for leaders who are humble and keep their pride in check, and is wary of those who fly too close to the sun.
He looks up to folks who are down-to-earth, who came from tougher backgrounds – those that had to fight their way to the top, and CEOs that live their product.
He was thrilled when I mentioned that Uber CEO Dara Khosrowshahi got behind the wheel as a driver last year.
“Exactly!
Mickey takes great pride in returning emails himself, spending time with new-hires, and being approachable.
Who stands out to Mickey as a leader he really respects?
Mickey immediately mentioned Andy Grove, the former CEO of Intel, and noted Mr. Grove’s book.
The name of that book?
“Only the Paranoid Survive.”
Enough said.
Mickey is quick to note that he never had a mentor, and that he had to learn to trust his own instincts.
He also learned early on that he had an ability to identify BS very quickly -- a skill he thinks is incredibly important for success.
He has a great admiration for leaders who are humble and keep their pride in check, and is wary of those who fly too close to the sun.
He looks up to folks who are down-to-earth, who came from tougher backgrounds – those that had to fight their way to the top, and CEOs that live their product.
He was thrilled when I mentioned that Uber CEO Dara Khosrowshahi got behind the wheel as a driver last year.
“Exactly!
Mickey takes great pride in returning emails himself, spending time with new-hires, and being approachable.
Who stands out to Mickey as a leader he really respects?
Mickey immediately mentioned Andy Grove, the former CEO of Intel, and noted Mr. Grove’s book.
The name of that book?
“Only the Paranoid Survive.”
Enough said.
Mickey’s Big Break
When Mickey was just 35-years-old, after a few years as a rising star at Bloomingdale’s and Macy’s, he was offered the job of running the clothing brand Ann Taylor.
The call caught Mickey off-guard, and he wasn’t even sure how they got his number or how they knew him.
He said no right away.
Why?
Well, he was just too conservative at that young age. He didn’t have much money, and feared taking a leap that may cause him to go broke.
Luckily for Mickey, he happened to be having dinner with New York executive Arthur Levitt Jr and told him the story of this clothing brand that had been trying to recruit him for months.
“Take the job!” Mr. Levitt proclaimed immediately.
He was the smartest person Mickey knew, was quite successful, and had the lifestyle Mickey wanted.
It was the nudge he needed.
Mickey took the job the following morning.
When Mickey was just 35-years-old, after a few years as a rising star at Bloomingdale’s and Macy’s, he was offered the job of running the clothing brand Ann Taylor.
The call caught Mickey off-guard, and he wasn’t even sure how they got his number or how they knew him.
He said no right away.
Why?
Well, he was just too conservative at that young age. He didn’t have much money, and feared taking a leap that may cause him to go broke.
Luckily for Mickey, he happened to be having dinner with New York executive Arthur Levitt Jr and told him the story of this clothing brand that had been trying to recruit him for months.
“Take the job!” Mr. Levitt proclaimed immediately.
He was the smartest person Mickey knew, was quite successful, and had the lifestyle Mickey wanted.
It was the nudge he needed.
Mickey took the job the following morning.
The Gap Comes Calling
One day in 1983, the phone rang.
It was Donald Fisher, the founder of The Gap.
Mickey was just 38-years-old, and The Gap has been long fledgling. It had 450 stores, $400M in sales, and profits were down to $20m and shrinking. It needed a change.
The two men began talking on-and-off for several months, and eventually the discussions turned to Mickey joining The Gap.
The thought of leaving the world he knew in New York City for The Gap’s corporate headquarters in San Francisco, or suddenly running a public company, didn’t intimidate Mickey.
Rather, he was worried what failure would do to him and his wife financially.
Again, those same overly-conservative thoughts that hold back so many entrepreneurs were creeping back in.
After the deal included a guarantee that would allow Mickey and his wife to secure adequate housing in New York if things didn’t work out, he was off to California to rebuild The Gap.
One day in 1983, the phone rang.
It was Donald Fisher, the founder of The Gap.
Mickey was just 38-years-old, and The Gap has been long fledgling. It had 450 stores, $400M in sales, and profits were down to $20m and shrinking. It needed a change.
The two men began talking on-and-off for several months, and eventually the discussions turned to Mickey joining The Gap.
The thought of leaving the world he knew in New York City for The Gap’s corporate headquarters in San Francisco, or suddenly running a public company, didn’t intimidate Mickey.
Rather, he was worried what failure would do to him and his wife financially.
Again, those same overly-conservative thoughts that hold back so many entrepreneurs were creeping back in.
After the deal included a guarantee that would allow Mickey and his wife to secure adequate housing in New York if things didn’t work out, he was off to California to rebuild The Gap.
Determination over Misery: Turning Gap Around
When Mickey took over The Gap, things were a mess.
The first two years were a complete nightmare for him – the worst period of his life.
He was miserable every single day, and he felt depressed like he never imagined possible.
He wished he wasn’t there, and thought he might be making a huge mistake.
But – he showed up every single day.
When I asked him why, Mickey quickly brought both hands up to the sides of his face, placed them next to his eyes, and mimicked the placement of blinders on a horse.
“I had a vision, and I was relentless. I had my warrior uniform on.”
Mickey explained that he put together a list of exactly what he wanted to do, and he would see that list through at all costs.
-a million colors, button-downs, sweatshirts in eight different colors, jean jackets, sweatpants, and eliminating all the low margin Levi's jeans.
“America needed a cool place to shop that was affordable” Mickey told me.
When Mickey left gap in 2002, it had 4,000 stores and revenue had grown to $14B.
It was one of the greatest turnaround stories in corporate American history.
I was in awe of the story, and the pain and out-of-this world determination it took for Mickey to get from 1983 to 2002.
I asked him to pick a characteristic that he most attributed his success to.
"You know the song writer, Diane Warren? There’s a great documentary."
What’s is called?
“Relentless”
When Mickey took over The Gap, things were a mess.
The first two years were a complete nightmare for him – the worst period of his life.
He was miserable every single day, and he felt depressed like he never imagined possible.
He wished he wasn’t there, and thought he might be making a huge mistake.
But – he showed up every single day.
When I asked him why, Mickey quickly brought both hands up to the sides of his face, placed them next to his eyes, and mimicked the placement of blinders on a horse.
“I had a vision, and I was relentless. I had my warrior uniform on.”
Mickey explained that he put together a list of exactly what he wanted to do, and he would see that list through at all costs.
-a million colors, button-downs, sweatshirts in eight different colors, jean jackets, sweatpants, and eliminating all the low margin Levi's jeans.
“America needed a cool place to shop that was affordable” Mickey told me.
When Mickey left gap in 2002, it had 4,000 stores and revenue had grown to $14B.
It was one of the greatest turnaround stories in corporate American history.
I was in awe of the story, and the pain and out-of-this world determination it took for Mickey to get from 1983 to 2002.
I asked him to pick a characteristic that he most attributed his success to.
"You know the song writer, Diane Warren? There’s a great documentary."
What’s is called?
“Relentless”
Mickey on Steve Jobs and The Apple Store
Mickey first met Steve Jobs at a friend's birthday party in Napa.
He had no idea that Jobs was determined to recruit him from that very first meeting.
Jobs told Mickey he wanted to “take Apple retail," and he knew Mickey had the eye to help create the Apple Store.
Mickey was hesitant, but after a year of non-stop attempts, Jobs promised Mickey he would join Gap’s Board if Mickey would join Apple’s.
Deal done. Jobs got his man.
It was 1999, and the two men got to work.
When Jobs showed Mickey the first design, Mickey told him right away he hated it.
I asked Mikey what he hated about it.
“If somebody has an ugly button on their shirt, it’s just ugly!”
Mickey wanted to see a simple design and a “less is more” approach.
The product had to be easy to see, and there needed to be white everywhere. It needed to be timeless.
Mickey also insisted on the actual store being fully built in a warehouse, so you can feel the full experience, windows and all.
Did Jobs push back?
No. He recruited Mickey for this exact reason. He backed down and let Mickey take the lead.
The two men got along beautifully, and Mickey looks back at Steve with great admiration.
When the Gap board was told in confidence that Mickey would soon be fired, Jobs immediately picked up the phone to let his friend know what was coming.
I asked Mickey what skill stood out most that made Steve great.
“He was extraordinarily fearless!”
Then Mickey paused, looked down:
“The world misses him”
Mickey first met Steve Jobs at a friend's birthday party in Napa.
He had no idea that Jobs was determined to recruit him from that very first meeting.
Jobs told Mickey he wanted to “take Apple retail," and he knew Mickey had the eye to help create the Apple Store.
Mickey was hesitant, but after a year of non-stop attempts, Jobs promised Mickey he would join Gap’s Board if Mickey would join Apple’s.
Deal done. Jobs got his man.
It was 1999, and the two men got to work.
When Jobs showed Mickey the first design, Mickey told him right away he hated it.
I asked Mikey what he hated about it.
“If somebody has an ugly button on their shirt, it’s just ugly!”
Mickey wanted to see a simple design and a “less is more” approach.
The product had to be easy to see, and there needed to be white everywhere. It needed to be timeless.
Mickey also insisted on the actual store being fully built in a warehouse, so you can feel the full experience, windows and all.
Did Jobs push back?
No. He recruited Mickey for this exact reason. He backed down and let Mickey take the lead.
The two men got along beautifully, and Mickey looks back at Steve with great admiration.
When the Gap board was told in confidence that Mickey would soon be fired, Jobs immediately picked up the phone to let his friend know what was coming.
I asked Mickey what skill stood out most that made Steve great.
“He was extraordinarily fearless!”
Then Mickey paused, looked down:
“The world misses him”
Mickey and the Work-From-Home World
I arrived for our meeting a few minutes early and watched Mickey passionately address his team at Alex Mill.
There he was in the center of the office, engaging everyone, asking questions, driving home his lessons.
He did the same during our meeting -- spontaneously calling people over, asking them questions, and popping into a nearby conference room after overhearing something that piqued his interest.
Mickey’s entire approach to the corporate world is the exact opposite of a work-from-home environment.
He told me companies need serendipity.
That breakthrough ideas come from collaboration, and in-person is essential to true learning and creating and maintaining company culture.
He said watching people make mistakes in real-time creates invaluable lessons that don’t happen otherwise.
Mickey even questions whether work-from-home was good for civilization as a whole, and chuckled as he told me about a large tech company that’s getting rid of office space entirely.
“How many of them are working!”
Is he totally closed to the idea forever?
Well, his team now has the option of working from home on Fridays.
I arrived for our meeting a few minutes early and watched Mickey passionately address his team at Alex Mill.
There he was in the center of the office, engaging everyone, asking questions, driving home his lessons.
He did the same during our meeting -- spontaneously calling people over, asking them questions, and popping into a nearby conference room after overhearing something that piqued his interest.
Mickey’s entire approach to the corporate world is the exact opposite of a work-from-home environment.
He told me companies need serendipity.
That breakthrough ideas come from collaboration, and in-person is essential to true learning and creating and maintaining company culture.
He said watching people make mistakes in real-time creates invaluable lessons that don’t happen otherwise.
Mickey even questions whether work-from-home was good for civilization as a whole, and chuckled as he told me about a large tech company that’s getting rid of office space entirely.
“How many of them are working!”
Is he totally closed to the idea forever?
Well, his team now has the option of working from home on Fridays.
Mickey on Fame
The Fortune Magazine cover, the notoriety, the fame.
Many seek that stuff – but for Mickey, it mostly just made him nervous.
It did nothing but raise the bar for Mickey, and reminded him what he had to live up to.
“Sometimes I wonder if I have imposter syndrome.”
Who doesn’t, Mickey. Who doesn’t.
The Fortune Magazine cover, the notoriety, the fame.
Many seek that stuff – but for Mickey, it mostly just made him nervous.
It did nothing but raise the bar for Mickey, and reminded him what he had to live up to.
“Sometimes I wonder if I have imposter syndrome.”
Who doesn’t, Mickey. Who doesn’t.
Mickey on What Motivates Him Today
Steve Jobs and Elon Musk biographer Walter Isaacson called Mickey “one of the few people in the world who were as successful and savvy as (Steve) Jobs on matters of design, image and consumer yearnings.”
Mickey ran Ann Taylor and The Gap.
He started Old Navy (he named it after a bar in Paris!)
He was at the help of J Crew.
Today he shows up every day running the Alex Mill clothing brand.
So why the heck is he still working.
“It never ends!”
He says he’s always trying to do better, and that at 79-years-old he’s better at creativity and detail than he’s ever been.
As he’s explaining this to me, he notices an Associate not far away, and calls her into the conference room area.
“How do you grade yourself after our conversation,” he asks her.
Mickey challenges her, they go back and forth – she holds her own. You can easily see the admiration they have for each other.
As she walks away, Mickey turns to me, and points back in the direction of the rest of the office.
“It’s about them.”
Then adds:
“And I love what I do. You have to.”
Steve Jobs and Elon Musk biographer Walter Isaacson called Mickey “one of the few people in the world who were as successful and savvy as (Steve) Jobs on matters of design, image and consumer yearnings.”
Mickey ran Ann Taylor and The Gap.
He started Old Navy (he named it after a bar in Paris!)
He was at the help of J Crew.
Today he shows up every day running the Alex Mill clothing brand.
So why the heck is he still working.
“It never ends!”
He says he’s always trying to do better, and that at 79-years-old he’s better at creativity and detail than he’s ever been.
As he’s explaining this to me, he notices an Associate not far away, and calls her into the conference room area.
“How do you grade yourself after our conversation,” he asks her.
Mickey challenges her, they go back and forth – she holds her own. You can easily see the admiration they have for each other.
As she walks away, Mickey turns to me, and points back in the direction of the rest of the office.
“It’s about them.”
Then adds:
“And I love what I do. You have to.”
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